4-bromo-N,N-dimethylbenzamide → 4-Bromo-N,N-dimethylbenzylamine

HRID 1484223Notes

Reaction equation

HRID 1484223 reaction equation
C[SiH](C)C1C=CC=CC=1[SiH](C)C.[CH3:13][N:14]([CH3:24])[C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:24][N:14]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][CH:21]=1)[CH3:13]

Participants

4

Reactant 2

HCID 1403894-bromo-N,N-dimethylbenzamideHCID 2733841HCID 2733841, compound

Product 1

HCID 2357574-Bromo-N,N-dimethylbenzylamineYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with argon atmosphere. Into the flask, iron complex A (1.0 mg, 0.002 mmol) was admitted as catalyst and dissolved in toluene (0.5 mL). To the solution, 1,2-bis(dimethylsilyl)benzene (475 μL) was added through a syringe, and N,N-dimethyl-4-bromobenzamide (228 mg, 1.0 mmol) was added. The solution was stirred at 100° C. for 30 minutes. Toluene was distilled off in vacuum. The crude product was purified by silica gel-packed column chromatography using hexane/ethyl acetate (20/1) as developing solvent, obtaining N,N-dimethyl-4-bromobenzylamine (184 mg, 0.86 mmol, 86%). The results are shown as Entry 2 in Table 5. The resulting amine was identified for geometry by 1H and 13C-NMR spectroscopy and IR spectroscopy.

Workup

  1. customA 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer
  2. temperaturewas heat
  3. customdried
  4. customwas purged with argon atmosphere
  5. distillationToluene was distilled off in vacuum
  6. customThe crude product was purified by silica gel-

Sources & evidence

ORD record
ord-6598e394847d4a7c8a5a59d72926b71f
Source dataset
uspto-grants-2016_08
Patent number
US09421532B2

Reaction notes

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